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Escuret, V ; Aucagne, V ; Joubert, N ; Durantel, D ; Rapp, KL ; Schinazi, RF ; Zoulim, F ; Agrofoglio, LA

Synthesis of 5-haloethynyl- and 5-(1,2-dihalo)vinyluracil-nucleosides : Antiviral activity and cellular toxicity

Bioorganic & Medicinal Chemistry 13 (21) 6015-6024

par Administrateur - publié le

Abstract :

In this article, we report the synthesis of hitherto unknown 5-haloethynyl and 5-(1,2-dihalo)vinyluracil nucleosides in the 2’-deoxy, 3’-deoxy- and ribosyl series, and we discuss their in vitro anti-HIV and anti-HCV activities and cellular toxicitites. As a result, on the basis of their selectivity index (SI) obtained with the HCV replicon system, but also on their cytotoxicity on peripheral blood mononuclear, CEM and VERO cell lines, the best compounds were the 5-bromoethynyluridine (SI = 3.2) and the 5-(1-chloro-2-iodo)vinyluridine (SI > 2.8). (c) 2005 Elsevier Ltd. All rights reserved.